Ecclesiastes: Confessions of a Wise Fool

Regret is a powerful and sometimes overwhelming feeling. But can hindsight and perspective turn regret into something better? The life of king Solomon answers us with a fairly confident "maybe!"

The book of Ecclesiastes shows us what it looks like for a wise person to look back on the things in life that cause them to feel regretful or cynical. In this book, we follow the character named Qoheleth (קֹהֶלֶת in Hebrew) - who seems to either be King Solomon or is at least meant to be similar to him (Ecclesiastes 1:12) - as he explores his thoughts about his life, his mistakes, and the meaning of it all. This book shows us a man who realizes that the good things in life can disappear in an instant, and that not even riches, power, and even wisdom itself can fully prevent injustice, loneliness, tragedy, and ultimately death.

Ecclesiastes is a challenging book because of how it questions the meaning of morality in light of mortality. If we are all going to die, what is the point of it all? Or, put another way, if I know that I am going to die one day, what should really matter to me? Some people see value in temporary things like wealth, social status, influence, and power - but even these things can be taken away suddenly by unforeseen circumstances in life, and ultimately everything is taken away from even the most powerful people at death. (Ecclesiastes 2:9-11)

In our own time, it is easy to look at the lives of those with more influence or "followers" than us and to feel like we are small and insignificant by comparison. It’s an easy temptation - to think that we might be happier if only we could get this or that, if only we could get recognition, or work for the right employer, find the right romantic partner, or whatever else. But these things come and go, here one minute and gone the next. All the wealth and fame in the world are not enough for true fulfillment.

Qoheleth gives us a gritty, honest, and grounded look at the meaning of life: sometimes, meaning and purpose elude us. Sometimes, life is just confusing and hard to pin down. But rather than leading to despair, Qoheleth promotes a surprisingly hopeful life philosophy: make the best of whatever situation you’re in, and take joy in the simple pleasures of life (Ecclesiastes 5:18-20). One day, God will clear away the confusion and frustration we face in this life, but until then we have to simply trust him and do what is right (Ecclesiastes 12:9-14).

Solomon was certainly one character in the Bible who shifted back and forth between being wise and foolish. He made all kinds of terrible choices alongside his good ones. What are we supposed to make of a life like that? More immediately, what do we think of our own lives, when we make a mix of good and bad choices? Ecclesiastes invites us to look at our lives in perspective, to understand the place of the good and the bad in our growing process, to understand that there is a time for everything, and ultimately to face the fact that we have a limited time to get our lives right. But rather than letting those thoughts cause us to be fearful, ashamed, and directionless, Ecclesiastes offers us the chance to be bold, to make the best of every day and every moment we have, and to remember that ultimately God's wisdom is the best way forward for our lives.

Letting go of our mistakes and weaknesses is a kind of freedom. Solomon had to learn the hard way that he couldn’t control everything, but we don’t have to. Wisdom is knowing our limitations and trusting that God knows how to run the world best. Peace is letting God take the weight of the world - and even our own lives - off our shoulders. Regret is no way to live. The way forward is trust, gratitude, love, and acceptance.


The following study questions include long reading selections, at least one from each chapter of Ecclesiastes. This is a very deep and sometimes intense book, and this study should be used to help you read the whole book through, even if it's over an extended period of time. So just know, this is not a short study!

  • Read Ecclesiastes 1:1-11. What emotions does this opening poem communicate to you? What does it say about life?
  • Read through Ecclesiastes chapter 2. What does this chapter say about fulfilment and purpose in life? Note especially verses 24-26. What do they say to you? Does this line up with other things you have read in the Bible?
  • Read through Ecclesiastes 3:9-22. This passage says a lot about cycles and repetition in life, as well as injustice, judgment, and death. What stands out to you the most? Try to describe in your own words how this passage describes life. What role does God play? What does it say about death?
  • Read Ecclesiastes 4:1-12. What does this passage say about the importance of human relationships? What different perspectives does this passage give on human interaction?
  • Read Ecclesiastes 5:8-20. What does this say about wealth, money, greed, and ambition? In what ways do you think these observations are applicable to our world today?
  • Read Ecclesiastes 6:1-6. What does this passage say about the sadness and "unfulfilment" of economically prosperous people? What does it say about not living life to the fullest? Do you think you can fully adopt this perspective for your life? Why or why not?
  • Read Ecclesiastes 7:13-25. Do you think the author means that wisdom is pointless, or that we have to be careful how much we trust our own wisdom? What picture does he paint of the human condition? What advice in this passage do you find that applies to you?
  • Read Ecclesiastes 8:7-15. What does this passage say about social structure, chaos, laws, crime, justice, injustice, and the relationship of all these things to the meaning of life? What part does God seem to play here?
  • Read Ecclesiastes 9:1-10. What surprising things does this passage say about sin, righteousness, and the fate of both good and bad people after death? How does this compare with what you know about common Christian beliefs about death?
  • Read Ecclesiastes 9:11-18. What does this passage say about "randomness" in life?
  • Skip this question if you are trying to get done quickly. Ecclesiastes 9:17-12:8 is one very long poem. Given what you have read in the rest of the book, take your time and think over the different sections of the poem. Do this at your own pace. What parts stand out to you?
  • Read the conclusion of the book in Ecclesiastes 12:9-14. Does this seem like a satisfying conclusion for you, or does it leave you wanting more? Does the idea of judgment by God give you hope or fear? How might judgment be a good thing, in light of the rest of this book?


Connect with a Christian Mentor!